Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:37:43 UTC

Update Date

2023-02-21 17:23:42 UTC

HMDB ID

HMDB0033854

Secondary Accession Numbers

HMDB33854

Metabolite Identification

Common Name

Isoprenyl alcohol

Description

Isoprenyl alcohol, also known as CH2=chc(CH3)2oh or methylbutenol, belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H). Isoprenyl alcohol is an earthy, herbal, and oily tasting compound. isoprenyl alcohol has been detected, but not quantified, in a few different foods, such as blackcurrants, citrus, and fruits. This could make isoprenyl alcohol a potential biomarker for the consumption of these foods. A tertiary alcohol that is 3-methylbut-1-ene carrying a hydroxy substituent at position 3.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,1-Dimethyl-2-propen-1-ol	ChEBI
1,1-Dimethyl-2-propenol	ChEBI
1,1-Dimethyl-2-propenyl alcoho	ChEBI
1,1-Dimethylallyl alcohol	ChEBI
2-Methyl but-3-ene-2-ol	ChEBI
2-Methyl-2-hydroxy-3-butene	ChEBI
2-Methyl-3-buten-2-ol	ChEBI
2-Methyl-3-buten-2-yl alcohol	ChEBI
3-Hydroxy-3-methyl-1-butene	ChEBI
3-Hydroxy-3-methylbutene	ChEBI
3-Methyl-1-buten-3-ol	ChEBI
alpha,alpha-Dimethylallyl alcohol	ChEBI
CH2=chc(CH3)2oh	ChEBI
Dimethylvinylcarbinol	ChEBI
Dimethylvinylmethanol	ChEBI
Methylbutenol	ChEBI
Vinyldimethylcarbinol	ChEBI
a,a-Dimethylallyl alcohol	Generator
Α,α-dimethylallyl alcohol	Generator
1, 1-Dimethyl-2-propenol	HMDB
1, 1-Dimethylallyl alcohol	HMDB
1,1-Dimethyl-2-propanol	HMDB
1,1-Dimethylallyl alchol	HMDB
2-Methyl-3-butene-2-ol	HMDB
2-Methylbut-3-en-2-ol	HMDB
3-Butyn-2-ol, 2-methyl- (8ci,9ci)	HMDB
3-Methyl-1-butene-3-ol	HMDB
3-Methyl-buten-(1)-ol-(3)	HMDB
3-Hydroxy-3-methylbutene, titanium salt	MeSH, HMDB
3-Hydroxy-3-methylbutene, tantalum salt	MeSH, HMDB
3-Hydroxy-3-methylbutene, aluminum salt	MeSH, HMDB
3-Hydroxy-3-methylbutene, geranium (4+) salt	MeSH, HMDB
3-Hydroxy-3-methylbutene, niobium (5+) salt	MeSH, HMDB
Isoprenyl alcohol	ChEBI

Chemical Formula

C₅H₁₀O

Average Molecular Weight

86.1323

Monoisotopic Molecular Weight

86.073164942

IUPAC Name

2-methylbut-3-en-2-ol

Traditional Name

3-buten-2-ol, 2-methyl-

CAS Registry Number

115-18-4

SMILES

CC(C)(O)C=C

InChI Identifier

InChI=1S/C5H10O/c1-4-5(2,3)6/h4,6H,1H2,2-3H3

InChI Key

HNVRRHSXBLFLIG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Hydrocarbon derivatives

Substituents

Tertiary alcohol
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

an alcohol (CPD-13614 )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0033854)
Cytoplasm (HMDB: HMDB0033854)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033854)

Source

Exogenous

Food

Food (HMDB: HMDB0033854)

Fruit

Berry

Citrus

Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0033854)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033854)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-28 °C	Not Available
Boiling Point	97.00 to 99.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1000 mg/mL	Not Available
LogP	0.892 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	29.4 g/L	ALOGPS
logP	1.2	ALOGPS
logP	0.91	ChemAxon
logS	-0.47	ALOGPS
pKa (Strongest Acidic)	17.84	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	26.48 m³·mol⁻¹	ChemAxon
Polarizability	10.07 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	116.219	31661259
DarkChem	[M-H]-	111.701	31661259
DeepCCS	[M+H]+	122.213	30932474
DeepCCS	[M-H]-	119.633	30932474
DeepCCS	[M-2H]-	155.849	30932474
DeepCCS	[M+Na]+	130.449	30932474
AllCCS	[M+H]+	121.1	32859911
AllCCS	[M+H-H2O]+	116.6	32859911
AllCCS	[M+NH4]+	125.3	32859911
AllCCS	[M+Na]+	126.5	32859911
AllCCS	[M-H]-	126.6	32859911
AllCCS	[M+Na-2H]-	131.3	32859911
AllCCS	[M+HCOO]-	136.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoprenyl alcohol	CC(C)(O)C=C	984.0	Standard polar	33892256
Isoprenyl alcohol	CC(C)(O)C=C	593.9	Standard non polar	33892256
Isoprenyl alcohol	CC(C)(O)C=C	595.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isoprenyl alcohol,1TMS,isomer #1	C=CC(C)(C)O[Si](C)(C)C	755.8	Semi standard non polar	33892256
Isoprenyl alcohol,1TBDMS,isomer #1	C=CC(C)(C)O[Si](C)(C)C(C)(C)C	986.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isoprenyl alcohol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0adl-9000000000-d70a3ec2038d4a4bacff	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoprenyl alcohol GC-MS (1 TMS) - 70eV, Positive	splash10-009f-9300000000-efc01b641b807f346e9a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoprenyl alcohol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00dl-9000000000-8dbe4fbdeca8fb3eb68e	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprenyl alcohol 10V, Positive-QTOF	splash10-014i-9000000000-86a9d9f2cfe6736f75f5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprenyl alcohol 20V, Positive-QTOF	splash10-014i-9000000000-1d12d0cf92a49c0e5205	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprenyl alcohol 40V, Positive-QTOF	splash10-0uxr-9000000000-832cf6ed4f4d38085021	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprenyl alcohol 10V, Negative-QTOF	splash10-000i-9000000000-91737f48e8c01dd76f40	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprenyl alcohol 20V, Negative-QTOF	splash10-00kr-9000000000-7258d8b666127480a11f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprenyl alcohol 40V, Negative-QTOF	splash10-014i-9000000000-5c162d0dd2c1dc8d99ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprenyl alcohol 10V, Positive-QTOF	splash10-014i-9000000000-50a1a2960709c5f19bef	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprenyl alcohol 20V, Positive-QTOF	splash10-014l-9000000000-a45a5647a91fd1bb55a8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprenyl alcohol 40V, Positive-QTOF	splash10-0uxr-9000000000-676ad0e6fda3b7b19775	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprenyl alcohol 10V, Negative-QTOF	splash10-000i-9000000000-2091e44a102d8284a813	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprenyl alcohol 20V, Negative-QTOF	splash10-000i-9000000000-16e831cea0512cdc6efd	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprenyl alcohol 40V, Negative-QTOF	splash10-0uxr-9000000000-7b6ecebd059861a614c8	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012034

KNApSAcK ID

C00035905

Chemspider ID

7959

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8257

PDB ID

Not Available

ChEBI ID

132752

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1040251

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Isoprenyl alcohol (HMDB0033854)

MOL for HMDB0033854 (Isoprenyl alcohol)

3D MOL for HMDB0033854 (Isoprenyl alcohol)

3D SDF for HMDB0033854 (Isoprenyl alcohol)

3D-SDF for HMDB0033854 (Isoprenyl alcohol)

PDB for HMDB0033854 (Isoprenyl alcohol)

3D PDB for HMDB0033854 (Isoprenyl alcohol)

SMILES for HMDB0033854 (Isoprenyl alcohol)

INCHI for HMDB0033854 (Isoprenyl alcohol)

Structure for HMDB0033854 (Isoprenyl alcohol)

3D Structure for HMDB0033854 (Isoprenyl alcohol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra